CN106103538B - Polymer and organic solar batteries comprising it - Google Patents
Polymer and organic solar batteries comprising it Download PDFInfo
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- CN106103538B CN106103538B CN201580015434.1A CN201580015434A CN106103538B CN 106103538 B CN106103538 B CN 106103538B CN 201580015434 A CN201580015434 A CN 201580015434A CN 106103538 B CN106103538 B CN 106103538B
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000011368 organic material Substances 0.000 claims description 19
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- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000005264 aryl amine group Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
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- 125000004104 aryloxy group Chemical group 0.000 claims description 12
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- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HLLICFJUWSZHRJ-UHFFFAOYSA-N tioxidazole Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)SC2=C1 HLLICFJUWSZHRJ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
- C08K3/041—Carbon nanotubes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
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Abstract
Description of the invention is related to polymer and the organic solar batteries including it.
Description
Technical field
The South Korea patent application 10-2014- submitted to Korean Intellectual Property Office the present invention claims on March 21st, 2014
No. 0033590 priority and right, entire contents are incorporated herein by reference.
The present invention relates to polymer and include its organic solar batteries.
Background technology
Organic solar batteries are the device that solar energy can be directly changed into electric energy by application photovoltaic effect.According to structure
Solar cell can be divided into inorganic solar cell and organic solar batteries at the material of film.Conventional solar cell by
It is made up of the p-n junction of doped crystalline silicon (Si) (it is by inorganic semiconductor).The electrons and holes diffusion generated by absorbing light
To any p-n junction, and electrode is moved to when by electric field acceleration.Power conversion efficiency during this is defined as supply to external electrical
The electrical power on road is worked as relative to the ratio between the solar power for entering solar cell and is standardizing virtual solar irradiation item at present
Efficiency has reached about 24% when being measured under part.However, since inorganic solar cell in the prior art is in economic feasibility
Limitation is shown with materials demand and supply side, and easy to process, cheap and organic semiconductor with several functions is too
Positive energy battery has become the focus of long-term alternative energy source.
For solar cell, it is important that improve efficiency to export more electric energy from solar energy as far as possible.In order to which this is carried
The efficiency of high solar battery, it is important that exciton as much as possible is generated inside semiconductor, but it is also important that lossless
Lost territory is by generated charge-extraction to outside.One of the reason of loss of charge, damages for generated electrons and holes because compound
Consumption.A variety of methods are had proposed so that generated electrons and holes are transmitted to electrode without loss, but are needed in most cases
Additional technique is wanted, and therefore may increase manufacturing cost.
Reference listing
Patent document
US 5331183
US 5454880
Invention content
Technical problem
The purpose of the present invention is to provide polymer and the organic solar batteries including it.
Technical solution
The present invention provides polymer comprising the unit indicated by following formula 1.
[formula 1]
In formula 1,
X1 and X2 are same or different to each other, and respectively stand alone as CRR ', NR, O, SiRR ', PR, S, GeRR ', Se or Te,
R and R ' are same or different to each other, and respectively stand alone as hydrogen；Deuterium；Halogen group；Itrile group；Nitro；Imide；Acyl
Amido；Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；It is substituted or is unsubstituted
Alkoxy；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；It is substituted or is unsubstituted
Artyl sulfo；The Alkylsulfinyl for being substituted or being unsubstituted；The Arylsulfinyl for being substituted or being unsubstituted；It is substituted
Or the alkenyl being unsubstituted；The silicyl for being substituted or being unsubstituted；The boryl for being substituted or being unsubstituted；It is substituted or not
The alkyl amine group being substituted；The aralkyl amido for being substituted or being unsubstituted；The arylamine group for being substituted or being unsubstituted；Through taking
Generation or the heteroaryl amido being unsubstituted；The aryl for being substituted or being unsubstituted；Or the heterocycle for being substituted or being unsubstituted,
R1 and R2 are same or different to each other, and respectively stand alone as deuterium；Halogen group；Itrile group；Nitro；Imide；Amide
Base；Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；The alkane for being substituted or being unsubstituted
Oxygroup；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；The virtue for being substituted or being unsubstituted
Base sulfenyl；The Alkylsulfinyl for being substituted or being unsubstituted；The Arylsulfinyl for being substituted or being unsubstituted；Be substituted or
The alkenyl being unsubstituted；The silicyl for being substituted or being unsubstituted；The boryl for being substituted or being unsubstituted；Be substituted or without
Substituted alkyl amine group；The aralkyl amido for being substituted or being unsubstituted；The arylamine group for being substituted or being unsubstituted；It is substituted
Or the heteroaryl amido being unsubstituted；The aryl for being substituted or being unsubstituted；Or the heterocycle for being substituted or being unsubstituted, and
A and B are same or different to each other, and respectively stand alone as the monocycle for being substituted or being unsubstituted or polycyclic arlydene；
Or the monocycle for being substituted or being unsubstituted or polycyclic divalent heterocycle.
In addition, the present invention provides organic solar batteries comprising：First electrode；Second electrode is arranged in face of the
One electrode；With one or more organic material layers, it is arranged between first electrode and second electrode and includes photoactive layer,
One or more layers of wherein organic material layer include above-mentioned polymer.
Advantageous effects
It is to be taken in precalculated position that the polymer of property embodiment, which has wherein R1 and R2, according to an example of the present invention
The regioregular in generation.The crystallinity of the polymer with regioregular of property embodiment according to an example of the present invention
It is relatively excellent.
In addition, for the polymer of property embodiment according to an example of the present invention, by including at least in addition to introducing
Also introduce A and B except the heterocycle of two N, be easy to control polymer band gap and/or highest occupied molecular orbital (HOMO) and
The energy level of lowest unoccupied molecular orbital (LUMO).
The polymer of property embodiment can be used as the organic of organic solar batteries according to an example of the present invention
The material of material layer, and include that its organic solar batteries can express out in raising open-circuit voltage and short circuit current and/or carry
The excellent characteristic of high efficiency etc..
According to an example of the present invention the polymer of property embodiment can be used alone in organic solar batteries or
To be used with the mixture of other materials, and expectable raising efficiency, and the characteristic (such as thermal stability) that passes through compound
The service life of intensifier.
Description of the drawings
Fig. 1 is the figure for illustrating the organic solar batteries of property embodiment according to an example of the present invention.
Fig. 2 is the figure of the high performance liquid chromatography (HPLC) for the compound for illustrating to prepare in embodiment 1.
Fig. 3 is the figure of the H NMR spectroscopy for the compound for illustrating to prepare in embodiment 1.
Fig. 4 is the figure of the UV spectrum for the polymer for illustrating to prepare in comparative example 1.
Fig. 5 is the figure of the electrochemical measurements (cyclic voltammetry) for the polymer for illustrating to prepare in comparative example 1.
Fig. 6 is the figure of the UV spectrum for the polymer for illustrating to prepare in embodiment 3.
Fig. 7 is the figure of the electrochemical measurements (cyclic voltammetry) for the polymer for illustrating to prepare in embodiment 3.
Fig. 8 is the figure of the UV spectrum for the polymer for illustrating to prepare in embodiment 4.
Fig. 9 is the figure of the electrochemical measurements (cyclic voltammetry) for the polymer for illustrating to prepare in embodiment 4.
Figure 10 be illustrate include the current density versus voltage of the organic solar batteries of the polymer of comparative example 1 figure.
Figure 11 be illustrate include the current density versus voltage of the organic solar batteries of the polymer of embodiment 2 figure.
Figure 12 be illustrate include the current density versus voltage of the organic solar batteries of the polymer of embodiment 3 figure.
The explanation of reference number and symbol
101：Substrate
102：First electrode
103：Hole transmission layer
104：Photoactive layer
105：Second electrode
Specific implementation mode
The present invention is described hereinafter.
In the present invention, " unit " means in polymer monomer included repetitive structure, and wherein monomer pass through it is poly-
Close the structure for being connected to polymer.
In the present invention, " including unit " means that the unit is included in the main chain of polymer.
There is the polymer of property embodiment wherein A to be arranged including at least two N's according to an example of the present invention
Between two heterocycles and R1 and R2 is away from the substituted regioregular in the positions of A relatively far away from.In the case, crystallinity
It is excellent.
Regioregular in the present invention means that substitution is selectively arranged in structure in the polymer with predetermined direction
Base.
In an example of the present invention embodiment, the band gap of the easily controllable polymer of structure by controlling A and B
And/or the energy level of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO).
In an example of the present invention embodiment, R1 and R2 are same or different to each other, and respectively stand alone as halogen radical
Group.
When R1 and R2 be halogen group when, by improve include the unit indicated by formula 1 polymer (its be through R1 and R2
Substitution) in the selectivity reacted can easily prepare compound, and the excellent crystallinity of prepared polymer, therefore can be improved
Charge mobility in organic electronic device (such as organic solar batteries, organic light emitting apparatus and organic transistor).
In addition, improving the absolute of highest occupied molecular orbital (HOMO) energy level of the polymer by introducing R1 and R2
Value, it is therefore intended that open-circuit voltage improves.
In an example of the present invention embodiment, A and B are as the electron donor in polymer.
When A and B is as electron donor, together with relatively expectable as the heterocycle of electron acceptor including X1 and X2
Push-pull effect (push-pull effect).In the case, due to forming low band gaps, and the position tool of the substituent group of R1 and R2
There are the predetermined party tropism based on A or B, the polymer that there is the charge mobility of excellent crystallinity and/or raising.
In an example of the present invention embodiment, A and B are same or different to each other, and wherein one or two or more
It is multiple to be each independently selected from lower structure.
In the structure,
B and c is respectively integer of 1 to 3,
The integer that d is 1 to 6,
The integer that e is 1 to 4,
X10 to X13 is same or different to each other, and respectively stands alone as CR3R4, NR3, O, SiR3R4, PR3, S, GeR3R4, Se
Or Te,
Y10 and Y11 are same or different to each other, and respectively stand alone as CR5, N, SiR5, P or GeR5, and
R3, R4, R5 and R100 are same or different to each other to R103, and respectively stand alone as hydrogen；Deuterium；Halogen group；Itrile group；
Nitro；Imide；Amide groups；Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；Through
The alkoxy for replacing or being unsubstituted；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；Through
The artyl sulfo for replacing or being unsubstituted；The Alkylsulfinyl for being substituted or being unsubstituted；The virtue for being substituted or being unsubstituted
Base sulfinyl；The alkenyl for being substituted or being unsubstituted；The silicyl for being substituted or being unsubstituted；It is substituted or is unsubstituted
Boryl；The alkyl amine group for being substituted or being unsubstituted；The aralkyl amido for being substituted or being unsubstituted；It is substituted or without taking
The arylamine group in generation；The heteroaryl amido for being substituted or being unsubstituted；The aryl for being substituted or being unsubstituted；Be substituted or not
The heterocycle being substituted.
In an example of the present invention embodiment, A and B are mutually the same.
In another exemplary embodiment, A and B are different from each other.
In an example of the present invention embodiment, A is
In an example of the present invention embodiment, the unit indicated by formula 1 is indicated by following formula 1-A.
[formula 1-A]
In formula 1-A,
X1, X2, R1, R2 and B are identical as those of restriction in formula 1,
X10 to X13 is same or different to each other, and respectively stands alone as CR3R4, NR3, O, SiR3R4, PR3, S, GeR3R4, Se
Or Te, and
R3, R4, R100 and R101 are same or different to each other, and respectively stand alone as hydrogen；Deuterium；Halogen group；Itrile group；Nitro；
Imide；Amide groups；Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；Be substituted or
The alkoxy being unsubstituted；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；Be substituted or
The artyl sulfo being unsubstituted；The Alkylsulfinyl for being substituted or being unsubstituted；The aryl sulfurous for being substituted or being unsubstituted
Acyl group；The alkenyl for being substituted or being unsubstituted；The silicyl for being substituted or being unsubstituted；The boron for being substituted or being unsubstituted
Base；The alkyl amine group for being substituted or being unsubstituted；The aralkyl amido for being substituted or being unsubstituted；It is substituted or is unsubstituted
Arylamine group；The heteroaryl amido for being substituted or being unsubstituted；The aryl for being substituted or being unsubstituted；Or it is substituted or without taking
The heterocycle in generation.
In an example of the present invention embodiment, B is
In another exemplary embodiment, B is
In another exemplary implementation scheme, B is
In an example of the present invention embodiment, the unit indicated by formula 1 is by following formula 2 to any one of formula 4 table
Show.
[formula 2]
[formula 3]
[formula 4]
In formula 2 to formula 4,
X1, X2, R1 and R2 are identical as those of restriction in formula 1,
X10 to X17 is same or different to each other, and respectively stands alone as CR3R4, NR3, O, SiR3R4, PR3, S, GeR3R4, Se
Or Te,
Y10 and Y11 are same or different to each other, and respectively stand alone as CR5, N, SiR5, P or GeR5, and
R3 to R5 and R100 to R105 is same or different to each other, and respectively stands alone as hydrogen；Deuterium；Halogen group；Itrile group；Nitre
Base；Imide；Amide groups；Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；Through taking
Generation or the alkoxy being unsubstituted；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；Through taking
Generation or the artyl sulfo being unsubstituted；The Alkylsulfinyl for being substituted or being unsubstituted；The aryl for being substituted or being unsubstituted
Sulfinyl；The alkenyl for being substituted or being unsubstituted；The silicyl for being substituted or being unsubstituted；It is substituted or is unsubstituted
Boryl；The alkyl amine group for being substituted or being unsubstituted；The aralkyl amido for being substituted or being unsubstituted；It is substituted or is unsubstituted
Arylamine group；The heteroaryl amido for being substituted or being unsubstituted；The aryl for being substituted or being unsubstituted；Be substituted or without
Substituted heterocycle.
The example of substituent group is described below, but not limited to this.
Term " substitution " means that the hydrogen atom for being connected to compound carbon atom is changed to other substituent groups, and to be replaced
Position without limitation, as long as the position be the substituted position of the hydrogen atom (that is, the commutable position of the substituent group) i.e.
Can, and when two or more are substituted, the two or more substituent group can be same or different to each other.
Term as used herein " be substituted or be unsubstituted " means through one or more substituent groups selected from the following
Substitution：Deuterium；Halogen group；Alkyl；Alkenyl；Alkoxy；Ester group；Carbonyl；Carboxyl；Hydroxyl；Naphthenic base；Silicyl；Aryl alkene
Base；Aryloxy group；Alkyl sulfenyl；Alkylsulfinyl；Arylsulfinyl；Boryl；Alkyl amine group；Aralkyl amido；Arylamine
Base；Heterocycle；Arylamine group；Aryl；Itrile group；Nitro；Hydroxyl；And heterocycle or unsubstituted.
Substituent group can be unsubstituted or be replaced with other substituent group.
In the present invention, halogen group can be fluorine, chlorine, bromine or iodine.
In the present invention, the carbon atom number of imide is not particularly limited, but preferably 1 to 25.Particularly, acid imide
Base can be the compound having following structure, but not limited to this.
In the present invention, for amide groups, one or two nitrogen of amide groups can through hydrogen, with 1 to 25 carbon atom
Straight chain, branch or cyclic alkyl or aryl substitution with 6 to 25 carbon atoms.Particularly, amide groups can be with following knot
The compound of structure formula, but not limited to this.
In the present invention, alkyl can be linear chain or branched chain, and its carbon atom number is not particularly limited, but preferably 1 to 50
It is a.Its specific example includes methyl, ethyl, propyl, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, tertiary butyl, Zhong Ding
Base, 1- methyl-butvls, 1- Ethyl-butyls, amyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- first
Base amyl, 2- methyl amyls, 4- methyl -2- amyls, 3,3- dimethylbutyls, 2- ethyl-butyls, heptyl, n-heptyl, 1- methyl
Hexyl, cyclopentyl-methyl, cyclohexyl methyl, octyl, n-octyl, t-octyl, 1- methylheptyls, 2- ethylhexyls, 2- propyl penta
Base, n-nonyl, 2,2- dimethyl heptyl, 1- Ethyl-propyls, 1,1- Dimethyl-propyls, isohesyl, 2- methyl amyls, 4- methyl
Hexyl, 5- methylhexyls etc., but not limited to this.
In the present invention, naphthenic base is not particularly limited, but the preferably naphthenic base with 3 to 60 carbon atoms, and it has
Body example includes cyclopropyl, cyclobutyl, cyclopenta, 3- methylcyclopentyls, 2,3- dimethylcyclopentyls, cyclohexyl, 3- methyl rings
Hexyl, 4- methylcyclohexyls, 2,3- Dimethylcyclohexyls, 3,4,5- trimethylcyclohexyls, 4- tetrabutyls cyclohexyl, suberyl,
Cyclooctyl etc., but not limited to this.
In the present invention, alkoxy can be straight chain, branch or cricoid.The carbon atom number of alkoxy is not particularly limited, but
Preferably 1 to 20.Its specific example includes methoxyl group, ethyoxyl, positive propoxy, isopropoxy (isopropoxy), isopropyl
It is base oxygroup (i-propyloxy), n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyl oxygen, different
Amoxy, positive hexyloxy, 3,3- dimethyl butyrates oxygroup, 2- ethyl-butoxies, n-octyloxy, positive nonyl epoxide, n-decyloxy, benzene first
Oxygroup, to methyl benzyloxy etc., but not limited to this.
In the present invention, alkenyl can be linear chain or branched chain, and its carbon atom number is not particularly limited, but preferably 2 to 40
It is a.Its specific example includes vinyl, 1- acrylic, isopropenyl, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- amylenes
Base, 2- pentenyls, 3- pentenyls, 3-methyl-1-butene base, 1,3- butadienyls, allyl, 1- phenyl vinyl -1- bases, 2-
Phenyl vinyl -1- bases, 2,2- diphenylacetylene -1- bases, 2- phenyl -2- (naphthalene -1- bases) ethylene -1- bases, 2,2- bis- (two
Phenyl -1- bases) ethylene -1- bases, Stilbene base, styryl (styrenyl) etc., but not limited to this.
In the present invention, the specific example of silicyl includes trimethyl silyl, triethylsilyl, tertiary butyl
Dimetylsilyl, vinyldimethylsilyl, propyl-dimethyl silicyl, triphenyl-silyl, diphenyl
Silicyl, phenyl silyl groups etc., but not limited to this.
In the present invention, aryl can be monocyclic aryl or polyaromatic, and include alkyl with 1 to 25 carbon atom or
Alkoxy with 1 to 25 carbon atom is the case where being substituted.In addition, the aryl in the present invention can refer to aromatic ring.
When aryl is monocyclic aryl, carbon atom number is not particularly limited, but preferably 6 to 25.The tool of monocyclic aryl
Body example includes phenyl, xenyl, terphenyl base etc., but not limited to this.
When aryl is polyaromatic, carbon atom number is not particularly limited, but preferably 10 to 24.The tool of polyaromatic
Body example include naphthalene, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc., but not limited to this.
In the present invention, fluorenyl can be substituted, and adjacent substituent group can be bonded to each other to form ring.
When fluorenyl is to be substituted, fluorenyl can be Deng.However, fluorenyl is without being limited thereto.
In the present invention, heterocycle be include one or more heterocycles as miscellaneous element in O, N and S atom, and its
Carbon atom number is not particularly limited, but preferably 2 to 60.The example of heterocycle includes thienyl, furyl, pyrrole radicals, imidazoles
Base, thiazolyl,Oxazolyl,Di azoly, triazolyl, pyridyl group, bipyridyl, pyrimidine radicals, triazine radical, triazolyl, acridine
Base, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine base, pyrrole
Piperazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo carbazole
It is base, benzothienyl, dibenzothiophene, benzofuranyl, phenanthroline, thiazolyl, differentOxazolyl,Di azoly, thiophene two
Oxazolyl, benzothiazolyl, phenothiazinyl, dibenzofuran group etc., but not limited to this.
Heterocycle can be monocycle or polycyclic, and can be the condensed ring of aromatic ring, alicyclic ring or aromatic ring and alicyclic ring.
In the present invention, the example of arylamine group includes the monoarylamine base for being substituted or being unsubstituted, is substituted or not
The diaryl amido being substituted or the triaryl amido for being substituted or being unsubstituted.Aryl in arylamine group can be monocycle virtue
Base or polyaromatic.Arylamine group including two or more aryl may include monocyclic aryl, polyaromatic or monocyclic aryl
Both with polyaromatic.
The specific example of arylamine group include aniline, naphthylamines, benzidine, anthranylamine, 3- metlyl-phenylamines, 4- methyl-naphthylamines,
2- methyl-biphens amine, 9- methyl-anthranylamine, hexichol amido, phenylnaphthalene amido, xylyl amido, phenyltoluene base amido, click
Azoles, triphenylamine base etc., but not limited to this.
In the present invention, the heteroaryl in heteroaryl amido can be selected from the example of above-mentioned heterocycle.
In the present invention, the aryl in aryloxy group, artyl sulfo, Arylsulfinyl and aralkyl amido and above-mentioned aryl
Example it is identical.Particularly, the example of aryloxy group includes phenoxy group, to toloxyl, toloxyl, 3,5- dimethyl-benzene
Oxygroup, 2,4,6- trimethylbenzenes oxygroup, to tert-butyl benzene oxygroup, 3- biphenylyloxies, 4- biphenylyloxies, 1- naphthoxys, 2- naphthalene oxygen
Base, 4- methyl-1s-naphthoxy, 5- methyl -2- naphthoxys, 1- anthracenes oxygroup, 2- anthracenes oxygroup, 9- anthracenes oxygroup, 1- phenanthrene oxygroup, 3- phenanthrene oxygen
The example of base, 9- phenanthrene oxygroups etc., artyl sulfo includes that thiophenyl, 2- methylphenyl-sulfanyls, 4- tert-butyl benzene sulfenyls etc. and aryl are sub-
The example of sulfonyl includes phenylsulfmyl, p-methylphenyl sulfinyl etc., but not limited to this.
In the present invention, the alkyl in alkyl sulfenyl and Alkylsulfinyl is identical as the example of abovementioned alkyl.Particularly, alkane
The example of base sulfenyl includes methylsulfany, ethylsulfanyl, tert. butyl-sulphenyl, hexyl sulfenyl, octylthio etc., and alkyl thionyl
The example of base includes mesyl, ethylsulfinyl-1 base, propyl sulfinyl, butylsulfinyl etc., but not limited to this.
In an example of the present invention embodiment, X1 S.
In another exemplary embodiment, X2 S.
In an example of the present invention embodiment, X10 S.
In another exemplary embodiment, X11 CR3R4.
In another exemplary implementation scheme of the present invention, X11 S.
In an example of the present invention embodiment, X12 O.
In an example of the present invention embodiment, X13 S.
In another exemplary embodiment, X14 S.
In another exemplary implementation scheme, X15 CR3R4.
In an example of the present invention embodiment, X16 O.
In another exemplary embodiment, X16 CR3R4.
In an example of the present invention embodiment, X17 S.
In an example of the present invention embodiment, Y10 CR5.
In another exemplary embodiment, X11 CR5.
In an example of the present invention embodiment, R100 is hydrogen.
In another exemplary embodiment, R101 is hydrogen.
In another exemplary embodiment, R102 is hydrogen.
In an example of the present invention embodiment, R103 is hydrogen.
In an example of the present invention embodiment, R104 is hydrogen.
In another exemplary embodiment, R105 is hydrogen.
In an example of the present invention embodiment, R3 is the branched alkyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R3 ' is 3, the 7- dimethyl octyls for being substituted or being unsubstituted.
In an example of the present invention embodiment, R3 3,7- dimethyl octyls.
In an example of the present invention embodiment, R3 is the aryl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R3 is the phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R3 is with the alkyl-substituted phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R3 is through alkyl-substituted phenyl.
In an example of the present invention embodiment, R3 is the phenyl replaced through hexyl.
In an example of the present invention embodiment, R4 is the branched alkyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R4 is 3, the 7- dimethyl octyls for being substituted or being unsubstituted.
In an example of the present invention embodiment, R4 3,7- dimethyl octyls.
In an example of the present invention embodiment, R4 is the aryl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R4 is the phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R4 is with the alkyl-substituted phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R4 is through alkyl-substituted phenyl.
In an example of the present invention embodiment, R4 is the phenyl replaced through hexyl.
In an example of the present invention embodiment, R5 is the heterocycle for being substituted or being unsubstituted.
In another exemplary embodiment, R5 is to be substituted or be unsubstituted including one or more S atoms
Heterocycle.
In another exemplary implementation scheme, R5 is the thienyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R5 be unsubstituted or through alkyl-substituted thienyl.
In an example of the present invention embodiment, R5 is through the alkyl-substituted thiophene with 1 to 30 carbon atom
Base.
In another exemplary implementation scheme of the invention, R5 is the thienyl replaced through 2- ethylhexyls.
In an example of the present invention embodiment, polymer includes by following formula 1-1 to any one of formula 1-3 tables
The unit shown.
[formula 1-1]
[formula 1-2]
[formula 1-3]
In formula 1-1 to 1-3,
The integer that n is 1 to 100000,
R1 and R2 are same or different to each other, and respectively stand alone as halogen group, and
R10 to R15 is same or different to each other, and respectively stands alone as the alkane for the linear chain or branched chain for being substituted or being unsubstituted
Base；The alkoxy for the linear chain or branched chain for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；Be substituted or without
Substituted aryl；Or the heterocycle for being substituted or being unsubstituted.
In an example of the present invention embodiment, R10 to R15 is same or different to each other, and be each independently through
The alkyl for replacing or being unsubstituted；Or the aryl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R10 is the branched alkyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R10 is 3, the 7- dimethyl octyls for being substituted or being unsubstituted.
In an example of the present invention embodiment, R10 3,7- dimethyl octyls.
In an example of the present invention embodiment, R11 is the branched alkyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R11 is 3, the 7- dimethyl octyls for being substituted or being unsubstituted.
In an example of the present invention embodiment, R11 3,7- dimethyl octyls.
In an example of the present invention embodiment, R12 is the branched alkyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R12 is 3, the 7- dimethyl octyls for being substituted or being unsubstituted.
In an example of the present invention embodiment, R12 3,7- dimethyl octyls.
In an example of the present invention embodiment, R12 is the aryl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R12 is the phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R12 is with the alkyl-substituted phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R12 is through alkyl-substituted phenyl.
In an example of the present invention embodiment, R12 is the phenyl replaced through hexyl.
In an example of the present invention embodiment, R12 is the heterocycle for being substituted or being unsubstituted.
In another exemplary embodiment, R12 is to be substituted or be unsubstituted including one or more S atoms
Heterocycle.
In another exemplary implementation scheme, R12 is the thienyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R12 be unsubstituted or through alkyl-substituted thienyl.
In an example of the present invention embodiment, R12 is through the alkyl-substituted thiophene with 1 to 30 carbon atom
Base.
In another exemplary implementation scheme of the invention, R12 is the thienyl replaced through 2- ethylhexyls.
In an example of the present invention embodiment, R13 is the branched alkyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R13 is 3, the 7- dimethyl octyls for being substituted or being unsubstituted.
In an example of the present invention embodiment, R13 3,7- dimethyl octyls.
In an example of the present invention embodiment, R13 is the aryl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R13 is the phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R13 is with the alkyl-substituted phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R13 is through alkyl-substituted phenyl.
In an example of the present invention embodiment, R13 is the phenyl replaced through hexyl.
In an example of the present invention embodiment, R13 is the heterocycle for being substituted or being unsubstituted.
In another exemplary embodiment, R13 is to be substituted or be unsubstituted including one or more S atoms
Heterocycle.
In another exemplary implementation scheme, R13 is the thienyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R13 be unsubstituted or through alkyl-substituted thienyl.
In an example of the present invention embodiment, R13 is through the alkyl-substituted thiophene with 1 to 30 carbon atom
Base.
In another exemplary implementation scheme of the invention, R13 is the thienyl replaced through 2- ethylhexyls.
In an example of the present invention embodiment, R14 is the aryl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R14 is the phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R14 is with the alkyl-substituted phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R14 is through alkyl-substituted phenyl.
In an example of the present invention embodiment, R14 is the phenyl replaced through hexyl.
In an example of the present invention embodiment, R15 is the aryl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R15 is the phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R15 is with the alkyl-substituted phenyl for being substituted or being unsubstituted.
In an example of the present invention embodiment, R15 is through alkyl-substituted phenyl.
In an example of the present invention embodiment, R15 is the phenyl replaced through hexyl.
In an example of the present invention embodiment, R1 is halogen group.
In another exemplary embodiment, R1 is fluorine.
In an example of the present invention embodiment, R2 is halogen group.
In another exemplary embodiment, R2 is fluorine.
In an example of the present invention embodiment, polymer is indicated by following formula 1-1-1 to formula 1-3-1.
[formula 1-1-1]
[formula 1-1-2]
[formula 1-1-3]
In an example of the present invention embodiment, the end group of polymer is heterocycle or aryl.
In an example of the present invention embodiment, the end group of polymer is 4- (trifluoromethyl) phenyl.
In an example of the present invention embodiment, the end group of polymer is bromo- thienyl.
In another exemplary embodiment, the end group of polymer is bromo- phenyl.
In another exemplary embodiment, the end group of polymer is trialkyl (thiophene -2- bases) stannyl.
Trialkyl in the present invention can be trimethyl or tributyl.
Property embodiment according to an example of the present invention, the number-average molecular weight of polymer be preferably 500g/mol extremely
1000000g/mol.Preferably, the number-average molecular weight of polymer is preferably 10000g/mol to 100000g/mol.In the present invention
An exemplary implementation scheme in, the number-average molecular weight of polymer is preferably 30000g/mol to 100000g/mol.
The molecular weight distribution of property embodiment according to an example of the present invention, polymer is 1 to 100.Preferably, it polymerize
The molecular weight distribution of object is 1 to 3.
Molecular weight distribution is lower and number-average molecular weight is higher, and electrical characteristics and mechanical property are better.
In addition, number-average molecular weight is preferably 100000g/mol or lower, so that polymer has predetermined or higher dissolving
Degree, and therefore can advantageously solution application method of administration.
Polymer is prepared based on following preparation example to be described.
Other than the polymer indicated by formula 1-1-1 and formula 1-2-1, the polymer for including the unit indicated by formula 1 can
Worked as by the monomer (wherein R1 is to be substituted-A-a heterocycles, and wherein R2 is substituted) and monomer B each 1 that are put into heterocycle
Amount, makes tris(dibenzylideneacetone) dipalladium (0) (Pd of 0.02 equivalent2(dba)3) and 0.08 equivalent triphenylphosphine and mixture
Reaction, and purify the product of gained and prepare.
Polymer according to the present invention can be reacted by multi-step chemical to be prepared.Reacted by alkylated reaction, Grignard,
Suzuki coupling reactions, Stille coupling reactions etc. prepare monomer, and then final polymer can be by C-C coupling reaction (such as
Stille coupling reactions) it prepares.When substituent group to be introduced is boric acid or boric acid ester compound, polymer can pass through Suzuki
It is prepared by coupling reaction, and when substituent group to be introduced is tributyl tin or tin trimethyl compound, polymer can pass through
Prepared by Stille coupling reactions, but method is without being limited thereto.
The exemplary implementation scheme of the present invention provides organic solar batteries comprising：First electrode；Second electricity
Pole, to be arranged to face first electrode；With one or more organic material layers, it is arranged in first electrode and second electrode
Between and include photoactive layer, one or more layers of wherein organic material layer include polymer.
Organic solar batteries according to an example of the present invention embodiment include first electrode, photoactive layer and
Second electrode.Organic solar batteries may also include substrate, hole transmission layer, and/or electron transfer layer.
In the exemplary implementation scheme of the present invention, when organic solar batteries receive photon from external light source,
Electrons and holes are generated between electron donor and electron acceptor.Generated hole is transmitted to anode by electron donor layer.
The present invention an exemplary implementation scheme in, organic material layer include hole transmission layer, hole injection layer or
The layer of the layer and hole transmission layer in simultaneous transmission and injection hole, hole injection layer or simultaneous transmission and injection hole includes poly-
Close object.
In another exemplary embodiment, organic material layer includes electron injecting layer, electron transfer layer or notes simultaneously
Enter and transmit the layer of electronics, and electron injecting layer, electron transfer layer or the layer of injection simultaneously and transmission electronics include polymer.
Fig. 1 is the figure for illustrating the organic solar batteries of property embodiment according to an example of the present invention.
In the exemplary implementation scheme of the present invention, when organic solar batteries receive photon from external light source,
Electrons and holes are generated between electron donor and electron acceptor.Generated hole is transmitted to anode by electron donor layer.
In the exemplary implementation scheme of the present invention, organic solar batteries may also include additional organic material
Layer.Organic solar batteries can reduce organic material layer therein by using having the organic material of multiple functions simultaneously
Number.
In the exemplary implementation scheme of the present invention, first electrode is anode, and second electrode is cathode.Another
In a exemplary implementation scheme, first electrode is cathode, and second electrode is anode.
The present invention an exemplary implementation scheme in, in organic solar batteries can with cathode, photoactive layer and
Anode is ranked sequentially, and being ranked sequentially with anode, photoactive layer and cathode, but it is without being limited thereto to put in order.
In another exemplary embodiment, in organic solar batteries, can also with anode, hole transmission layer,
Photoactive layer, electron transfer layer and cathode are ranked sequentially, and can also be with cathode, electron transfer layer, photoactive layer, hole
Transport layer and anode are ranked sequentially, but it is without being limited thereto to put in order.
In the exemplary implementation scheme of the present invention, organic solar batteries, which have, just sets structure.
In the exemplary implementation scheme of the present invention, organic solar batteries have inverted structure.
In the exemplary implementation scheme of the present invention, organic solar batteries have cascaded structure.
The organic solar batteries of property embodiment can have one or two or more according to an example of the present invention
A photoactive layer.
In another exemplary embodiment, buffer layer may be provided between photoactive layer and hole transmission layer or light
Between active layer and electron transfer layer.In the case, hole injection layer can also be provided between anode and hole transmission layer.This
Outside, electron injecting layer can also be provided between cathode and electron transfer layer.
In the exemplary implementation scheme of the present invention, photoactive layer includes one selected from electron donor and electron acceptor
Kind or two or more, and electron donor material includes polymer.
The present invention an exemplary implementation scheme in, electron acceptor material can be selected from fullerene, fullerene derivate,
Bathocuproine, semiconductor simple substance, semiconducting compound, and combinations thereof.Particularly, in electron acceptor material it is one kind selected from the following
Or two or more compounds：Fullerene, fullerene derivate ((6,6)-phenyl-C61- butyric acid-methyl esters (PCBM) or (6,
6)-phenyl-C61- butyric acid-cholesteryl ester (PCBCR)), polybenzimidazoles (PBI) and 3,4,9,10-- tetracarboxylic acids it is double-
Benzimidazole (PTCBI).
In the exemplary implementation scheme of the present invention, electron donor and electron acceptor constitute bulk heterojunction (BHJ).
Bulk heterojunction means that electron donor material and electron acceptor material are mixed with each other in photoactive layer.
In the exemplary implementation scheme of the present invention, it includes that N-shaped organic material layer and p-type are organic that photoactive layer, which has,
The double-layer film structure of material layer, and p-type organic material layer includes polymer.
In the present invention, substrate can be the glass with excellent transparency, surface smoothness, handlability and water-resisting property
Substrate or transparent plastic substrate, but not limited to this, as long as and substrate is commonly used in organic solar batteries.It has
Body example include glass, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP),
Polyimides (PI), tri acetyl cellulose (TAC) etc., but not limited to this.
Anode can be made of transparent and with excellent conductive material, but not limited to this.The example includes：Metal, such as
Vanadium, chromium, copper, zinc and gold or its alloy；Metal oxide, such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxygen
Compound (IZO)；The combination of metal and oxide, such as ZnO:Al or SnO2:Sb；Conducting polymer, such as poly- (3 methyl thiophene) gather
[3,4- (ethylidene -1,2- dioxy) thiophene] (PEDOT), polypyrrole and polyaniline etc., but not limited to this.
Formed anode method be not particularly limited, but anode can for example by using sputtering, electron beam, heat deposition, spin coating,
Screen painting, ink jet printing, blade coating or gravure printing method are applied on a surface of substrate, or by coating film forming form
It is formed.
When forming anode on substrate, anode can undergo cleaning, remove moisture removal and hydrophilically modified technique.
For example, patterned ito substrate continuously uses detergent, acetone and isopropanol (IPA) cleaning, then in heat
It is 1 to 30 minute dry at 100 to 150 DEG C on plate, it is 10 minutes dry preferably at 120 DEG C, to remove moisture removal, and when substrate is complete
When all clear is clean, substrate surface is through hydrophilically modified.
It is modified by above-mentioned surface, the level for the surface potential that knot surface potential maintains suitable for photoactive layer can be made.This
Outside, during modification, thin polymer film can easily form on anode, and the quality of film also can be improved.
The preconditioning technique example of anode includes the surface oxidation method for a) using parallel plate type to discharge, b) by vacuum shape
Method under state by using the ozone oxidation surface of UV (ultraviolet light) generations, c) using free by oxygen caused by plasma
The oxidizing process etc. of base.
It can be according to one of the state selection method of anode or substrate.However, in all methods, it is preferably prevented from oxygen and is detached from sun
The surface of pole or substrate, and farthest inhibit moisture and organic material residual.In the case, pretreated essence can be made
Effect maximizes.
As specific example, the method by using the ozone oxidation surfaces generated UV can be used.In the case, through figure
The ito substrate of case is toasted on hot plate after ultrasonic clean and is fully dried, and is then introduced into room, and can be passed through and be operated UV
Lamp makes the patterned ito substrate of ozone clean that oxygen is generated with UV light reactions.
However, the surface modifying method of patterned ito substrate is limited without special in the present invention, and can be used any
Method, as long as this method is the method on oxidase substrate surface.
Cathode can be the metal with low work function, but not limited to this.Its specific example includes：Metal, as magnesium, calcium, sodium,
Potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead or its alloy；Or multilayer material, such as LiF/Al, LiO2/Al、LiF/Fe、
Al:Li、Al:BaF2And Al:BaF2:Ba, but not limited to this.
Cathode can be in display 5x10-7It deposits and is formed in the hot vaporizer of support or lower vacuum degree, but forming method is not
It is limited to the method.
Hole transmission layer and/or electron transport layer materials are effectively shifting the electrons and holes detached from photoactive layer
To electrode, and material is not particularly limited.
Hole transport layer material can be poly- (3,4- the ethyldioxythiophenes) (PEDOT for adulterating poly- (styrene sulfonic acid)：
) and molybdenum oxide (MoO PSSx)；Vanadium oxide (V2O5)；Nickel oxide (NiO)；With tungsten oxide (WOx) etc., but not limited to this.
Electron transport layer materials can be electron extraction metal oxide, and its specific example includes the metal of 8-hydroxyquinoline
Complex；Including Alq3Complex；Metal complex including Liq；LiF；Ca；Titanium oxide (TiOx)；Zinc oxide (ZnO)；With
Cesium carbonate (Cs2CO3) etc., but not limited to this.
Photoactive layer can by by light active material (such as electron donor and/or electron acceptor) dissolving in organic solvent,
Then solution is applied by the method for such as spin coating, dip-coating, screen painting, spraying, blade coating and brushing by is formed, but formation side
Method is without being limited thereto.
Invention pattern
In following Preparations and embodiment, the preparation method of polymer and the organic solar batteries including it will be described
Manufacture.However, the following example is provided for illustrating the present invention, and the scope of the present invention is not limited thereto.
The synthesis of 1. monomer A of embodiment
By the bis- bromo- 5- fluorobenzene of 4,7- of 3.1195g (10mmol) simultaneously [c] [1,2,5] thiadiazoles (FBTBr2)、4.2116g
The monomer of the introducing stannyl (Sn) of (4mmol), tris(dibenzylideneacetone) dipalladium (0) (Pd of 0.733g (0.08mmol)2
(dba)3) triphenylphosphine of catalyst and 0.084g (0.32mmol) is put into flask, so that mixture is deaerated, then adds thereto
The toluene of 100ml, and the mixture of gained is made to be reacted 48 hours at 80 DEG C.It is mixed by being extracted with dichloromethane after reaction
It closes object, remove solvent under reduced pressure, and in hexane:Dichloromethane=4:Raw product is set to carry out silica column under 1 ratio
Purifying obtains final product.(dark solid, yield：35%)
Fig. 2 is the figure of the high performance liquid chromatography (HPLC) for the compound for illustrating to prepare in embodiment 1.
Fig. 3 is the figure of the H NMR spectroscopy for the compound for illustrating to prepare in embodiment 1.
The synthesis of 2. formula 1-1-1 of embodiment
By the monomer of the embodiment 1 of 1mmol, the electron donor monomer for having been introduced into Sn of 1mmol, 0.02mmol three (two
BENZYLIDENE ACETONE) two palladiums (0) (Pd2(dba)3) and the triphenylphosphine of 0.08mmol be put into microwave special container, then make mixture
Deaerate 5 minutes three times.
Then, the drying dimethylformamide (DMF) of the dry toluene and 1mL of 20mL is added thereto, and mixture is 120
It reacts 10 minutes at DEG C, is reacted 10 minutes at 140 DEG C, and reacted 1 hour at 150 DEG C, then is cooled to room temperature, thereto
End-capping reagent is added, and gained mixture reacts 1 hour at 150 DEG C.
After reaction, reaction solution in methanol and 1M hydrochloric acid (HCl) 1:It precipitates in 1 solution, then filters, by filtering
Polymer is dissolved in chlorobenzene, by the solution of dissolving and ethylenediamine tetra-acetic acid (EDTA)+water (H2O it) mixes, and the mixing of gained
Object reacts 2 hours at 100 DEG C.After reacting, it detaches organic layer and washes with water, it is then clear again with 3 weight % acetic acid again
It washes twice, and is cleaned again with 5% potassium fluoride, the polymer solution of acquisition is then made to carry out chromatography over silica.
After column chromatography, by precipitating products therefrom in methyl alcohol, resulting polymers powder being put into Soxhlet sets
Pipe purifies products therefrom with the sequence of methanol, acetone, hexane and chloroform, then makes the part being dissolved in chloroform in methyl alcohol
It precipitates, then filtering precipitate obtains final polymer.
The synthesis of 3. formula 1-2-1 of embodiment
By the monomer of the embodiment 1 of 1mmol, the electron donor monomer for having been introduced into Sn of 1mmol, 0.02mmol three (two
BENZYLIDENE ACETONE) two palladiums (0) (Pd2(dba)3) and the triphenylphosphine of 0.08mmol be put into microwave special container, then make mixture
Deaerate 5 minutes three times.
Then, the drying dimethylformamide (DMF) of the dry toluene and 1mL of 20mL is added thereto, and mixture is 120
It reacts 10 minutes at DEG C, is reacted 10 minutes at 140 DEG C, and reacted 1 hour at 150 DEG C, then is cooled to room temperature, thereto
End-capping reagent is added, and gained mixture reacts 1 hour at 150 DEG C.
After reacting, reaction solution in methanol and 1M hydrochloric acid (HCl) 1:It precipitates in 1 solution, then filters, will filter
Polymer be dissolved in chlorobenzene, by the solution of dissolving and ethylenediamine tetra-acetic acid (EDTA)+water (H2O it) mixes, and gained is mixed
Object is closed to react 2 hours at 100 DEG C.After reacting, it detaches organic layer and washes with water, then cleaned again with 3 weight % acetic acid
Twice, and again it is cleaned with 5% potassium fluoride, the polymer solution of acquisition is then made to carry out chromatography over silica.
After column chromatography, by precipitating products therefrom in methyl alcohol, resulting polymers powder being put into Soxhlet sets
Pipe purifies products therefrom with the sequence of methanol, acetone, hexane and chloroform, then makes the part being dissolved in chloroform in methyl alcohol
It precipitates, then filtering precipitate obtains final polymer.
Fig. 6 is the figure of the UV spectrum for the polymer for illustrating to prepare in embodiment 3.
Fig. 7 is the figure of the electrochemical measurements (cyclic voltammetry) for the polymer for illustrating to prepare in embodiment 3.
The synthesis of 4. formula 1-3-1 of embodiment
The monomer of embodiment 1 and the electron donor monomer for having been introduced into Sn are put into microwave special container.In argon environment to
Wherein add three-o-tolyl phosphines and tris(dibenzylideneacetone) dipalladium (0) (Pd2(dba)3), generate vacuum state, and to its
The dimethylformamide (DMF) of the toluene and 1ml of middle addition 10ml.
Then, reaction carries out 5 minutes at 130 DEG C, carries out 5 minutes at 140 DEG C, is carried out 30 minutes at 150 DEG C, and
It is carried out at 160 DEG C 30 minutes 1 hour, then adds Br- benzotrifluorides thereto, and gained mixture reacts 5 at 30 DEG C
Minute, it reacts 5 minutes at 140 DEG C, is reacted 30 minutes at 150 DEG C, and reacted 30 minutes 1 hour at 160 DEG C.
After reacting, reaction solution precipitates in the solution of methanol and 2M hydrochloric acid (HCl), washes with water organic layer, so
Chlorobenzene is used to carry out column chromatography at high temperature afterwards.
After column chromatography, by precipitating products therefrom in methyl alcohol and making to be obtained with methanol, acetone, hexane and chloroform
Polymer powder carry out Soxhlet extractions, obtain the polymer compound of the formula 1-3-1 of 447.7mg.
Number-average molecular weight (Mn)：25600g/mol
Molecular weight distribution (PDI)：1.22
Fig. 8 is the figure of the UV spectrum for the polymer for illustrating to prepare in embodiment 4.
Fig. 9 is the figure of the electrochemical measurements (cyclic voltammetry) for the polymer for illustrating to prepare in embodiment 4.
The synthesis of 1. formula 1-1-2 of comparative example
The bis- bromo- 5- fluorobenzene of 4,7- of 1mmol simultaneously [c] [1,2,5] thiadiazoles (FBTBr2) monomer, 1mmol have been introduced into Sn
Monomer, 0.02mmol tris(dibenzylideneacetone) dipalladium (0) (Pd2(dba)3) and 0.08mmol triphenylphosphine be put into it is micro-
Wave special container, and mixture is made to deaerate 5 minutes three times.
Then, the drying dimethylformamide (DMF) of the dry toluene and 1mL of 20mL is added thereto, and mixture is 120
It reacts 10 minutes at DEG C, is reacted 10 minutes at 140 DEG C, and reacted 1 hour at 150 DEG C, then is cooled to room temperature, thereto
End-capping reagent is added, and gained mixture reacts 1 hour at 150 DEG C.
After reacting, reaction solution in methanol and 1M hydrochloric acid (HCl) 1:It precipitates in 1 solution, then filters, will filter
Polymer be dissolved in chlorobenzene, the solution of dissolving is mixed with ethylenediamine tetra-acetic acid (EDTA)+water (H2O), and gained is mixed
Object is closed to react 2 hours at 100 DEG C.After reacting, it detaches organic layer and washes with water, it is then clear with 3 weight % acetic acid again
It washes twice, and is cleaned again with 5% potassium fluoride, the polymer solution of acquisition is then made to carry out chromatography over silica.
After column chromatography, by precipitating products therefrom in methyl alcohol, resulting polymers powder being put into Soxhlet sets
Pipe purifies products therefrom with the sequence of methanol, acetone, hexane and chloroform, then makes the part being dissolved in chloroform in methyl alcohol
It precipitates, then filtering precipitate obtains final polymer.
Fig. 4 is the figure for illustrating the UV spectrum by the formula 1-1-2 polymer indicated.
Fig. 5 is the figure of the electrochemical measurements (cyclic voltammetry) for the polymer for illustrating to prepare in comparative example 1.
Embodiment 1 to 6 and comparative example 1 to 9
By using prepared polymer as electron donor and PC70BM is set as electron acceptor, while by mixing ratio
The value (w/w ratios) being set in the following table 1, and mixture is dissolved in dichloro-benzenes (DCB) and prepares composite solution.In such case
Under, concentration is adjusted to 2.0 weight %, and organic solar batteries are made with ITO/PEDOT:PSS/ photoactive layers/Al
Structure.It is cleaned by ultrasonic the glass substrate being coated with through ITO using distilled water, acetone and 2- propyl alcohol, the surfaces ozone treatment ITO is used in combination
It 10 minutes, is then heat-treated 5 minutes at 235 DEG C and in the PEDOT of 4000rpm spin coatings 45nm thickness:PSS (AI4083) 40 seconds.
In order to be coated with photoactive layer, with 0.45 μm of PP syringe filters filtration compounds-PCBM composite solution and spin coating, then lead to
It crosses using hot vaporizer 3 × 10-8Depositing Al manufactures organic solar batteries to 100nm thickness under the vacuum of support.
The light transfer characteristic of the organic solar batteries manufactured in above-mentioned experimental example and comparative example is in 100mW/cm2
Under conditions of measure, be as a result illustrated in the following table 1.
Table 1
In table 1, VOC、JSC, FF and PCE be respectively intended to mean open-circuit voltage, short circuit current, fill factor and energy conversion effect
Rate.Open-circuit voltage and short circuit current are respectively X-axis intercept and Y intercept in four quadrants of voltage-current density curve, and
As the two values increase, the efficiency of organic solar batteries preferably improves.In addition, fill factor is by will be in curve
Value obtained by the area divided by open-circuit voltage of the rectangle of drafting and the product of short circuit current.Energy conversion efficiency can be worked as these three
It is obtained when value divided by the intensity of radiant light, and higher value is preferred.
From the result of table 1, confirm that the polymer of property embodiment according to an example of the present invention can be used as having
The material of machine solar cell, and can confirm that polymer has regioregular, thus better than poly- without regioregular
The case where closing object.
Figure 10 be illustrate include the current density versus voltage of the organic solar batteries of the polymer of comparative example 1 figure.
Figure 11 be illustrate include the current density versus voltage of the organic solar batteries of the polymer of embodiment 2 figure.
Figure 12 be illustrate include the current density versus voltage of the organic solar batteries of the polymer of embodiment 3 figure.
Claims (14)
1. a kind of polymer, it includes the units indicated by following formula 1-A：
[formula 1-A]
In formula 1-A,
X1 and X2 are same or different to each other, and respectively stand alone as CRR ', NR, O, SiRR ', PR, S, GeRR ', Se or Te,
R and R ' are same or different to each other, and respectively stand alone as hydrogen；Deuterium；Halogen group；Itrile group；Nitro；Imide；Amide groups；
Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；The alcoxyl for being substituted or being unsubstituted
Base；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；The aryl for being substituted or being unsubstituted
Sulfenyl；The Alkylsulfinyl for being substituted or being unsubstituted；The Arylsulfinyl for being substituted or being unsubstituted；It is substituted or not
The alkenyl being substituted；The silicyl for being substituted or being unsubstituted；The boryl for being substituted or being unsubstituted；It is substituted or without taking
The alkyl amine group in generation；The aralkyl amido for being substituted or being unsubstituted；The arylamine group for being substituted or being unsubstituted；Be substituted or
The heteroaryl amido being unsubstituted；The aryl for being substituted or being unsubstituted；Or the heterocycle for being substituted or being unsubstituted,
R1 and R2 are same or different to each other, and respectively stand alone as deuterium；Halogen group；Itrile group；Nitro；Imide；Amide groups；Hydroxyl
Base；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；The alkoxy for being substituted or being unsubstituted；
The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；The aryl sulphur for being substituted or being unsubstituted
Base；The Alkylsulfinyl for being substituted or being unsubstituted；The Arylsulfinyl for being substituted or being unsubstituted；Be substituted or without
Substituted alkenyl；The silicyl for being substituted or being unsubstituted；The boryl for being substituted or being unsubstituted；It is substituted or is unsubstituted
Alkyl amine group；The aralkyl amido for being substituted or being unsubstituted；The arylamine group for being substituted or being unsubstituted；It is substituted or not
The heteroaryl amido being substituted；The aryl for being substituted or being unsubstituted；Or the heterocycle for being substituted or being unsubstituted, and
B is selected from the one or two or more of lower structure：
In the structure,
B and c is respectively integer of 1 to 3,
The integer that d is 1 to 6,
The integer that e is 1 to 4,
X10 to X13 is same or different to each other, and respectively stand alone as CR3R4, NR3, O, SiR3R4, PR3, S, GeR3R4, Se or
Te,
Y10 and Y11 are same or different to each other, and respectively stand alone as CR5, N, SiR5, P or GeR5, and
R3, R4, R5 and R100 are same or different to each other to R103, and respectively stand alone as hydrogen；Deuterium；Halogen group；Itrile group；Nitro；
Imide；Amide groups；Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；Be substituted or
The alkoxy being unsubstituted；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；Be substituted or
The artyl sulfo being unsubstituted；The Alkylsulfinyl for being substituted or being unsubstituted；The aryl sulfurous for being substituted or being unsubstituted
Acyl group；The alkenyl for being substituted or being unsubstituted；The silicyl for being substituted or being unsubstituted；The boron for being substituted or being unsubstituted
Base；The alkyl amine group for being substituted or being unsubstituted；The aralkyl amido for being substituted or being unsubstituted；It is substituted or is unsubstituted
Arylamine group；The heteroaryl amido for being substituted or being unsubstituted；The aryl for being substituted or being unsubstituted；Or it is substituted or without taking
The heterocycle in generation.
2. polymer according to claim 1, wherein R1 and R2 are same or different to each other, and respectively stand alone as halogen radical
Group.
3. polymer according to claim 1, wherein B is as electron donor.
4. polymer according to claim 1, wherein the unit indicated by formula 1-A is by appointing in such as following formula 2 to formula 4
One indicates：
[formula 2]
[formula 3]
[formula 4]
In formula 2 to formula 4,
X1, X2, R1 and R2 are identical as those of restriction in formula 1-A,
X10 to X17 is same or different to each other, and respectively stand alone as CR3R4, NR3, O, SiR3R4, PR3, S, GeR3R4, Se or
Te,
Y10 and Y11 are same or different to each other, and respectively stand alone as CR5, N, SiR5, P or GeR5, and
R3 to R5 and R100 to R105 is same or different to each other, and respectively stands alone as hydrogen；Deuterium；Halogen group；Itrile group；Nitro；
Imide；Amide groups；Hydroxyl；The alkyl for being substituted or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；Be substituted or
The alkoxy being unsubstituted；The aryloxy group for being substituted or being unsubstituted；The alkyl sulfenyl for being substituted or being unsubstituted；Be substituted or
The artyl sulfo being unsubstituted；The Alkylsulfinyl for being substituted or being unsubstituted；The aryl sulfurous for being substituted or being unsubstituted
Acyl group；The alkenyl for being substituted or being unsubstituted；The silicyl for being substituted or being unsubstituted；The boron for being substituted or being unsubstituted
Base；The alkyl amine group for being substituted or being unsubstituted；The aralkyl amido for being substituted or being unsubstituted；It is substituted or is unsubstituted
Arylamine group；The heteroaryl amido for being substituted or being unsubstituted；The aryl for being substituted or being unsubstituted；Or it is substituted or without taking
The heterocycle in generation.
5. polymer according to claim 1, wherein the polymer includes by any one in such as following formula 1-1 to formula 1-3
The unit of expression：
[formula 1-1]
[formula 1-2]
[formula 1-3]
In formula 1-1 to formula 1-3,
The integer that n is 1 to 100000,
R1 and R2 are same or different to each other, and respectively stand alone as halogen group, and
R10 to R15 is same or different to each other, and respectively stands alone as the alkyl for the linear chain or branched chain for being substituted or being unsubstituted；Through
The alkoxy of linear chain or branched chain for replacing or being unsubstituted；The naphthenic base for being substituted or being unsubstituted；It is substituted or is unsubstituted
Aryl；Or the heterocycle for being substituted or being unsubstituted.
6. polymer according to any one of claim 1 to 5, wherein the number-average molecular weight of the polymer is 500g/
Mol to 1000000g/mol.
7. polymer according to any one of claim 1 to 5, wherein the molecular weight distribution of the polymer be 1 to
100。
8. a kind of organic solar batteries, it includes：
First electrode；
It is set as the second electrode in face of the first electrode；And
It is arranged between the first electrode and the second electrode and includes one or more organic materials of photoactive layer
Layer,
One of them or more organic material layer includes polymer according to any one of claim 1 to 5.
9. organic solar batteries according to claim 8, wherein the organic material layer includes hole transmission layer, hole
Implanted layer or simultaneous transmission and the layer for injecting hole, and
The hole transmission layer, the hole injection layer or the simultaneous transmission and the layer for injecting hole include the polymer.
10. organic solar batteries according to claim 8, wherein the organic material layer includes electron injecting layer, electricity
Sub- transport layer or the layer for injecting and transmitting electronics simultaneously, and
The electron injecting layer, the electron transfer layer or the layer of described while injection and transmission electronics include the polymer.
11. organic solar batteries according to claim 8, wherein the photoactive layer includes to be selected from electron donor and electricity
The one or two or more of sub- receptor, and
The electron donor includes the polymer.
12. organic solar batteries according to claim 11, wherein the electron acceptor is selected from fullerene, fullerene spreads out
Biology, carbon nanotube, carbon nano tube derivative, bathocuproine, semiconductor simple substance, semiconducting compound, and combinations thereof.
13. organic solar batteries according to claim 11, wherein the electron donor and the electron acceptor are constituted
Bulk heterojunction (BHJ).
14. organic solar batteries according to claim 8, wherein the photoactive layer, which has, includes N-shaped organic material
The double-layer film structure of layer and p-type organic material layer, and
The p-type organic material layer includes the polymer.
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| KR20140033590 | 2014-03-21 | ||
| KR10-2014-0033590 | 2014-03-21 | ||
| PCT/KR2015/002655 WO2015142067A1 (en) | 2014-03-21 | 2015-03-19 | Polymer and organic solar cell comprising same |
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| EP (1) | EP3121211B1 (en) |
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| US11063219B2 (en) * | 2016-03-29 | 2021-07-13 | Sumitomo Chemical Company, Limited | Organic photoelectric conversion element, and solar cell module and sensor provided with the same |
| CN107452897B (en) * | 2016-05-31 | 2020-03-17 | 清华大学 | Preparation method and preparation device of organic thin-film solar cell |
| KR102130193B1 (en) * | 2017-06-27 | 2020-07-03 | 주식회사 엘지화학 | Organic solar cell |
| KR102542194B1 (en) * | 2017-09-12 | 2023-06-12 | 주식회사 엘지화학 | Compound and organic electronic device comprising the same |
| KR102250385B1 (en) * | 2017-10-18 | 2021-05-11 | 주식회사 엘지화학 | Organic photodiode and organic image sensor comprising the same |
| KR102410122B1 (en) * | 2017-11-17 | 2022-06-16 | 주식회사 엘지화학 | Heterocyclic compound and organic solar cell comprising the same |
| KR20200116363A (en) | 2019-04-01 | 2020-10-12 | 삼성전자주식회사 | Compound and photoelectric device, image sensor and electronic device including the same |
| GB2589570A (en) | 2019-11-29 | 2021-06-09 | Sumitomo Chemical Co | Photoactive composition |
| JP2021127398A (en) * | 2020-02-14 | 2021-09-02 | 住友化学株式会社 | Polymer, composition, ink, and photoelectric conversion element |
| TWI734564B (en) * | 2020-07-21 | 2021-07-21 | 國立中興大學 | Perovskite solar cells and method for producing the same |
| CN111883660A (en) * | 2020-08-26 | 2020-11-03 | 中国科学院重庆绿色智能技术研究院 | Fluorinated fused ring electron acceptor-based oligomer small-molecule solar cell and preparation method thereof |
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| KR101725622B1 (en) | 2017-04-11 |
| TWI603992B (en) | 2017-11-01 |
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| EP3121211A4 (en) | 2017-11-01 |
| WO2015142067A1 (en) | 2015-09-24 |
| KR20150110363A (en) | 2015-10-02 |
| US20170077405A1 (en) | 2017-03-16 |
| CN106103538A (en) | 2016-11-09 |
| JP6408023B2 (en) | 2018-10-17 |
| JP2017509750A (en) | 2017-04-06 |
| EP3121211B1 (en) | 2021-02-24 |
| EP3121211A1 (en) | 2017-01-25 |
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